Piperidine → (1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(piperidine-1-carbonyl)piperidin-1-yl)methanone

HRID 83603

Reaction equation

HRID 83603 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:4][CH:3]=1.C(N=C=NCCCN(C)C)C.O[N:41]1[C:45]2C=[CH:47][CH:48]=[CH:49][C:44]=2N=N1.C(N(CC)C(C)C)(C)C.N1CCCCC1>C(Cl)Cl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([N:18]2[CH2:19][CH2:20][CH:21]([C:24]([N:41]3[CH2:47][CH2:48][CH2:49][CH2:44][CH2:45]3)=[O:25])[CH2:22][CH2:23]2)=[O:17])=[CH:27][CH:28]=1

Participants

9

Reactant 5

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 573857961-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid

Product 1

HCID 57385555(1-(4-chlorobenzyl)-1H-indol-2-yl)(4-(piperidine-1-carbonyl)piperidin-1-yl)methanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(1-(4-chlorobenzyl)-1H-indole-2-carbonyl)piperidine-4-carboxylic acid (100 mg, 0.252 mmol), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (97 mg, 0.504 mmol), and 1-Hydroxybenzotriazole (68 mg, 0.504 mmol) were dissolved in 3.0 mL of DCM. The reaction was allowed to stir for 10 minutes before N,N-Diisopropylethylamine (88 μL, 0.504 mmol) and piperidine (50 μL, 0.504 mmol) were added. The reaction was allowed to stir overnight. The reaction was diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with another aliquot of water. The ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude material was purified in silica gel using the gradient 100% hexanes to 50% ethyl acetate:hexanes. Yield: 86 mg (White solid)

Workup

  1. additionwere added
  2. customThe layers were separated
  3. washthe organic layer was washed with another aliquot of water
  4. washThe ethyl acetate layer was washed with saturated citric acid, saturated sodium bicarbonate, and saturated sodium chloride
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified in silica gel using the gradient 100% hexanes to 50% ethyl acetate

Sources & evidence

ORD record
ord-012cf44d51d24568a07d6d13bc6a4045
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Linked notes

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